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While the Flecktones performed together for the first time in 1988 during an episode of the Lonesome Pine Special, in a 1992 interview, Fleck traces the formation of the band to 1987:

I met Howard Levy at the Winnipeg Folk Festival in 1987... Someone introduced us and said, You guys have to play together.' We sat down and started playing one evening after the show and ended up playing all night. We never really talked - we just played. And it was incredible. I couldn't believe some of the things he could do. As for the Wootens, they come from a family in Virginia Beach where there are five brothers who are all marvelous musicians. They had a family band that played a lot of Motown - the Jacksons and so forth. They also played a lot of funk. And they played some jazz. I was sitting at home one day, and I got this telephone call out of the blue. It was Victor Wooten. I had never met him nor heard of him. He said, 'Hi, I like your music and I just want to play for you a little bit.' He played bass over the phone, and I couldn't believe what I was hearing. He played things that sounded like banjo-stuff, on the electric bass. Victor introduced me to his brother, Roy, a drummer who was working on a new instrument. It was around that time I got a call to do a TV program for the 'Lonesome Pine' series, in Kentucky. They asked me to put together my own avant-garde banjo show. So I called all of these guys and put them together to do this show. That was the beginning."[1]

Following their performance on Lonesome Pine Special, the Flecktones played 9 tour dates during November 1989.[2]

Following the brief tour, the band recorded their first album, the self-titled Bela Fleck and the Flecktones in February 1990. The album was received well. Critic Geoffrey Himes wrote, "Fleck's banjo-playing takes the quartet on wide tangents through the outer space of jazz improvisation and minimalist composition, but he always brings them back to the traditions of rural America".[3] Himes also praised Harmonica-player Howard Levy as the star of the album.

In March 1990, the band began an extensive year of touring that would become characteristic of the band moving forward. The quartet received attention for their musical innovations and invention, including praise from music critic Bill Kolhaase. However, he was critical of the band's lack of a drum kit, claiming that Wooten's "electronic beat seemed a bit muddy compared to the real thing".[4]

1991 saw another year of extensive touring and another new album. On June 2, 1991, the Flecktones released their second album, Flight of the Cosmic Hippo. Like their previous album, Cosmic Hippo was received favorably. Himes applauded for their use of their prodigious improvisatory ability.[5] John Griffin of The Gazette also praised the group's ability to create such an individual style that "the whole of idea of style disappears."[6] Mike Joyce, of the Washington Post was impressed by the Flecktones' unique sound and ability to maintain a distinct voice and personality. In a review of one of their concerts, Joyce called a Flecktones show a "musical free-for-all, embracing the band's recorded material and venturing off into the great unknown the next." [7]

Once again, the Flecktones toured extensively in 1992, and in August, released their third album, UFO Tofu. UFO Tofu was another successful album. Jim Santella of the Buffalo News praised the band's mastery of styles and their ability to weave together complicated pieces. Santella even compared Fleck's playing to a "miniature Bach canon."[8]

UFO Tofu would be the last album the Flecktones recorded with their original lineup intact. Howard Levy, the band's harmonica, keyboard player left the band in December 1992. While the departure of Levy was tough for the band, it was not unfounded. During their 1992 tour it became evident to the band that Levy was not happy with the rigors of touring, and wanted to spend more time with his wife and children.[9]

The remaining trio, consisting of Fleck and the Wooten brothers, recorded their fourth album, Three Flew Over the Cuckoo's Nest. "'Once we started rehearsing, everything was fine,' said Fleck. ‘We started finding ways to sound good, and it was real exciting.'" Critic Alan Sculley remarks on how without Levy, the band loses some its "pop appeal", but on the other hand, with their new trio, all three musicians have more room to show off their chops. Sans Levy, the Flecktones, as usual spent most of 1993 on the road and released Three Flew Over the Cuckoo's Nest in September of that year.[10]

In July 1996 the Flecktones released their fifth album, and first live album, Live Art. Devoted fans who had been seeing the band for several years were clamoring for an album to capture the experience of live Flecktones, and this album fit the bill. The trio even took home a Grammy for Best Pop Instrumental Performance in 1997 for the track "Sinister Minister" off of the album.

In April 1997, the Flecktones became a quartet again, as they added saxophone player Jeff Coffin to the mix. Coffin would remain in the band from 1997 until 2008.[11]

1997 saw more collaborations with big-name jam bands. In June, the Flecktones opened for The Dave Matthews Band, which drew rave reviews.[12] In July the Flecktones toured Europe and sat in on the second set of a Phish show in Lyon, France. This marked the second and final time that the Flecktones played with Phish.[13]

In June 1998, the Flecktones released their sixth album, and fifth studio album, Left of Cool. Left of Cool represents a switch from previous Flecktones albums, as the band, according to critic Terri Horak "jettisoned their self imposed rule to only record what could be duplicated on live instruments."[14] While some, including Horak praised the new musical directions the band was going, others, Geoffrey Himes remarked that Left of Cool sounded too ordinary. In his negative review he wrote, "Unfortunately the Flecktones' first studio album in five years reveals that they've become a very ordinary band."[15] Himes adds, "The four Flecktones are all marvelous musicians, and they come up with imaginative parts for the new album's 15 cuts. The overall concept, however has diminished into easy-to-digest pop-jazz, for which there is too much already." [16]

In July 2000, the Flecktones released their eighth album, Outbound. Outbound is another studio album, and again the Flecktones' philosophy with this album was to do something different from everything they had done before.[17] What makes Outbound unique is the way in which the Flecktones recorded the album. The quartet recorded each track on the album, then invited guest musicians to overdub vocals or instrumentation. Outbound guests include: Jon Anderson from Yes, Shawn Colvin and John Medeski, of Medeski, Martin and Wood, to name a few.[18] The album earned the Flecktones the Grammy for Best Contemporary Jazz Album that year.

Live at the Quick, which was also released as a DVD, is the band's ninth album, and second live album. For fans of live Flecktones, this album, like Live Art, successfully captured the sound and feel of the Flecktones in concert.[19]

Little Worlds, the band's tenth album was released on August 12, 2003. Like previous Flecktones' albums, Little Worlds features a slew of musical guests, from Sam Bush on mandolin, Derek Trucks on guitar and even former New York Yankee and guitarist Bernie Williams works his way into a track. Little Worlds was released as a 3-CD album, but for the less committed listener, the band also released Ten From Little Worlds, which includes ten songs off of the original 3-CD Little Worlds.

In February 2006, the band released their eleventh album, The Hidden Land. As with every Flecktones album, they needed to change something from their last album. For The Hidden Land, the Flecktones didn't want any guest musicians. "'The truth is, the last few records are not what we are,' Fleck said. ‘Obviously, we loved playing with those musicians, but if you keep on doing it, you become a gathering point rather than a group with its own identity.'"[20] For the Flecktones to keep moving forward, they felt their music had to get back to the roots of the quartet.[21]

Hidden Land received mixed reviews. Critic Michael Endelman of Entertainment Weekly, wrote that the Flecktones sound "hasn't aged well."[22] Dan Ouelette of Billboard found Hidden Land to be "by far their best album." Ouelette was particularly impressed by the quartet's range of repertoire in this album.[23]

After spending much of the year apart, the Flecktones came together in 2008 to release a holiday album, Jingle All the Way. Jingle All the Way was received well. Geoffrey Himes praised the band for being able to package the Flecktones' complex sound into an easily digestible holiday album, without having to compromise the band's quintessential Flecktone sound.[24]

Jingle All The Way would turn out to be the Flecktones' last album with saxophone player Jeff Coffin. After the death of Dave Matthews Band saxophone player LeRoi Moore, Coffin went on to become the sax player for Matthews. To replace Coffin, the band decided to bring Howard Levy back into the fold. Levy returned to the Flecktones in the summer of 2011 for a brief tour and to record a new album, Rocket Science. Rocket Science is the Flecktones' fourteenth album, and fourth with Howard Levy. Fans of the Flecktones' first three albums were thrilled to hear Levy's return to the fold. Jeff Kelman of Jazz Times writes favorably about Rocket Science and Levy's reunion with the Flecktones, "Rocket Science recaptures everything that made the Flecktones so fresh, so innovative, so important during its first five years."[25] Kelman particularly praised the album's writing and the interactions between Levy and Fleck. Allmusic critic Thom Jurek also gave Rocket Science a rave review, "Rocket Science fires on all cylinders and comes off as a fresh and exciting reintroduction to a newly energized Flecktones."[26]

In June 2012, following another summer tour, the Flecktones announced their hiatus as a band. In a statement sent to their fans through the Flecktones mailing list, the band announced their indefinite hiatus. The statement reads:

It's been a phenomenal year for the band. We came back together to make a new recording (Rocket Science on E1) and to tour for a year, and we certainly did both of those things to the fullest extent possible. Having Howard Levy brought back the wild and unruly energy- and combustion- that the original line-up always had. But now 18 years later – we're all grown up, so it was a very new experience for us, as well. The shows went through the roof, and I can't think of one that didn't go great. You guys came out and supported our efforts, bringing us the final element that we needed to ensure that the magic would occur. I feel that the band hit new heights in cohesion, and group improv, and individual musical achievement. And we had a great time while doing it.

As the tour wound down towards the end of our time together, we began to consider when we would do this again. And everyone was eager for that to happen. But it will likely be several years til we can marshall the flecktone forces again, due to the rich and varied lives and careers that everyone has developed through the years. I do invite you to follow us each separately, because I think everyone is doing wonderful things. And I look forward to the next time when the Flecktones play together again, Best regards to all-